Although the first recorded ski run on Hollyburn was down a large, snow-covered debris pile at the abandoned Nasmyth mill in January, 1925, it is very likely that Scandinavian skiers had been skiing on the plateau above, or even from the peak of Hollyburn, before then. By 1928, a well-established run had been cleared from Hollyburn Peak to First Lake. Skiers who enjoyed the challenges of steeper terrain spent much of their time on the peak to shoulder run. Even more popular was the run from the Hollyburn shoulder to the plateau which, at some point, became known as Romstads run. Hollyburn's ski pioneers did not have the luxury of today's shaped skis, high-speed lifts and groomed trails. This limited the number of runs one could make in a day and required a special set of skills. Novices were encouraged to join one of the local ski clubs - the Hollyburn Pacific Ski Club or the Vancouver Ski Club - where they could receive instruction from more advanced skiers and compete in races on all three of the North Shore mountains; Hollyburn, Grouse, and Seymour.

The first cross-country skiers appeared on Hollyburn in 1925. Beginning in the early 1930's, downhill skiing became more popular. With the development of downhill ski runs on Mount Strachan and Black Mountain in the 1970's, cross-country skiers returned to Hollyburn Mountain.

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